Antimicrobial flavonoids and diterpenoids from Dodonaea angustifolia

Omosa, Leonidah Kerubo; Amugune, Beatrice; Ndunda, Beth; Milugo, Trizah K.; Heydenreich, Matthias; Yenesew, Abiy; Midiwo, Jacob O.

doi:10.1016/j.sajb.2013.11.012

Cited by 44 publications

(48 citation statements)

References 22 publications

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“…Alternative routes to furan formation have been proposed, and involve the formation and subsequent loss of a 9,13epoxy bridge in conjunction with an additional oxidation of C-15 or C-16 (Henderson and McCrindle, 1969;Zerbe et al, 2014). It seems, however, that the presence of the C-9 hydroxyl (and by extension the 9,13-epoxy bridge) is not essential for furan or lactone ring formation as multiple furan-and lactone-bearing diterpenoids without C-9 hydroxylation exist (Smith et al, 1982;Omosa et al, 2014;Anwar et al, 2017). Nevertheless, a potential intermediate of this alternative route was identified in the present study as a major product of VacTPS2 when coupled with VacTPS1 (3a), and similar compounds are often encountered in other furan/lactone diterpenoid-producing species (Ono et al, 1999;Tesso and K€ onig, 2004;Kulkarni et al, 2013).…”

Section: Identification Of a Cyp Capable Of Peregrinol Oxidationmentioning

confidence: 99%

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

et al. 2018

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Summary Vitex agnus‐castus L. (Lamiaceae) is a medicinal plant historically used throughout the Mediterranean region to treat menstrual cycle disorders, and is still used today as a clinically effective treatment for premenstrual syndrome. The pharmaceutical activity of the plant extract is linked to its ability to lower prolactin levels. This feature has been attributed to the presence of dopaminergic diterpenoids that can bind to dopamine receptors in the pituitary gland. Phytochemical analyses of V. agnus‐castus show that it contains an enormous array of structurally related diterpenoids and, as such, holds potential as a rich source of new dopaminergic drugs. The present work investigated the localisation and biosynthesis of diterpenoids in V. agnus‐castus. With the assistance of matrix‐assisted laser desorption ionisation‐mass spectrometry imaging (MALDI‐MSI), diterpenoids were localised to trichomes on the surface of fruit and leaves. Analysis of a trichome‐specific transcriptome database, coupled with expression studies, identified seven candidate genes involved in diterpenoid biosynthesis: three class II diterpene synthases (diTPSs); three class I diTPSs; and a cytochrome P450 (CYP). Combinatorial assays of the diTPSs resulted in the formation of a range of different diterpenes that can account for several of the backbones of bioactive diterpenoids observed in V. agnus‐castus. The identified CYP, VacCYP76BK1, was found to catalyse 16‐hydroxylation of the diol‐diterpene, peregrinol, to labd‐13Z‐ene‐9,15,16‐triol when expressed in Saccharomyces cerevisiae. Notably, this product is a potential intermediate in the biosynthetic pathway towards bioactive furan‐ and lactone‐containing diterpenoids that are present in this species.

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Section: Identification Of a Cyp Capable Of Peregrinol Oxidationmentioning

confidence: 99%

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

et al. 2018

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“…The avonoids S-sakuranetin, naringenin, 3-O-methylgalangin and 7-O-methyl-eriodictiol were the main phenolic constituents reported so far from the exudate [2,3] which showed important DPPH scavenging activity [3]. Furthermore, several methoxy-avone derivatives such as quercetin O-methyl ether derivatives showed interesting biological activities such as antioxidant [4], antibacterial [5], antihypercholesterolemic [6] and anti-in ammatory activities [7]. We report in this paper the structure of 3′,4′,5-trihydroxy-3,7-dimethoxy avone (3,7-di-O-methylquercetin) a further methyl avonol isolated from this plant, which is a di-O-methyl derivative of quercetin, a common avonoid present in many fruits and vegetables.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3′,4′,5-trihydroxy-3,7-dimethoxyflavone, C₁₇H₁₄O₇

Brito

Simirgiotis

Jerz

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…It was reported that hautriwaic acid lactone (21) and pinocembrin (74) showed inhibitory activity against Saccharomyces cerevisiae (Omosa et al 2014). Parvitexin B, parvitexin C, scaparvin B and scaparvin A (14, 16-18) were reported with phytotoxic activity on root growth ).…”

Section: Other Activitiesmentioning

confidence: 99%

Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities

et al. 2016

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Furanoditerpenoids are a special group of diterpenoids composing of one or more furan rings, which are rarely found in nature. This review aims to survey the various naturally occurring furanoditerpenoids and their pharmacological activities. A fairly large number of furanoditerpenoids have been reported from the families Euphorbiaceae, Fabaceae and Lamiaceae, and a few ones from the families Asteraceae, Codoniaceae, Dioscoreaceae, Fossombroniaceae, Jamesoniellaceae, Meliaceae, Menispermaceae, Olacaceae, Psathyrellaceae, Sapindaceae and Scapaniaceae. Their distribution correlates strongly with the taxonomic divisions. Most of these plants are widely used in traditional medicines, and furanoditerpenoids have therefore been disclosed with a wide range of bioactivities including anti-cancer, antiinflammation and anti-microorganism. To structure this review, the furanoditerpenoids were classified into seven types, including clerodane-type (Type I), labdane-type (Type II), cassane-type (Type III), abietane-type (Type IV), spongian-type (Type V), prenylbisabolane-type (Type VI) and miscellaneous type (Type VII). On the basis of 170 references, this review covers the distribution, phytochemistry, synthesis and pharmacological activities of furanoditerpenoids, describing 444 compounds. The information provided in this review might shed light on further research and development of furanoditerpenoids as potential therapeutic agents.

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Antimicrobial flavonoids and diterpenoids from Dodonaea angustifolia

Cited by 44 publications

References 22 publications

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

Crystal structure of 3′,4′,5-trihydroxy-3,7-dimethoxyflavone, C₁₇H₁₄O₇

Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities

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Antimicrobial flavonoids and diterpenoids from Dodonaea angustifolia

Cited by 44 publications

References 22 publications

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus

Crystal structure of 3′,4′,5-trihydroxy-3,7-dimethoxyflavone, C17H14O7

Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities

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Crystal structure of 3′,4′,5-trihydroxy-3,7-dimethoxyflavone, C₁₇H₁₄O₇